Structure-activity relationship of procyanidins on advanced glycation end products formation and corresponding mechanisms

Chen, Yuanyuan; Tang, Shimiao; Chen, Yashu; Zhang, Roujie; Zhou, Mengzhou; Wang, Chao; Feng, Nianjie; Wu, Qian

doi:10.1016/j.foodchem.2018.08.090

Cited by 57 publications

(23 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Structural diversity has been postulated to be an important element affecting the antioxidant activities of flavonoids. Some studies have compared the antioxidant activities of flavonoid subclasses with different structures [13][14][15][16][17] In the current study, the procyanidin B2, epicatechin, epigallocatechin, taxifolin, quercetin, and rutin were selected. These six flavonoids possessed similar chemical structures, and the differences in the chemical structures were displayed in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

“…Structural diversity has been postulated to be an important element affecting the antioxidant activities of flavonoids. Some studies have compared the antioxidant activities of flavonoid subclasses with different structures [ 13 , 14 , 15 , 16 , 17 ]: (1) The position and number of hydroxyl groups greatly affect the antioxidant activities of flavonoids. (2) The antioxidant activities of flavonoids are dependent on the degree of polymerization.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Comparison of In Vitro and In Vivo Antioxidant Activities of Six Flavonoids with Similar Structures

et al. 2020

View full text Add to dashboard Cite

The in vitro and in vivo antioxidant activities of six flavonoids with similar structures, including epicatechin (EC), epigallocatechin (EGC), procyanidin B2 (P), quercetin (Q), taxifolin (T), and rutin (R) were compared. The structures of the six flavonoids and their scavenging activities for 2,2-diphenyl-1-picrylhydrazyl (DPPH•) and 2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS+) radicals were closely related. The flavonoids decreased serum contents of malondialdehyde (MDA) and nitric oxide (NO), and increased serum total antioxidative capacity (T-AOC), superoxide dismutase (SOD), catalase (CAT), and glutathione peroxidase (GSH-Px) levels to different degrees in d-galactose-treated mice. The changes in mRNA expression of liver GSH-Px1, CAT, SOD1, and SOD2 by d-galactose were dissimilarly restored by the six flavonoids. Moreover, the six flavonoids differentially prevented the inflammatory response caused by oxidative stress by inhibiting interleukin (IL)-1β, IL-6, and tumor necrosis factor (TNF)-α levels, and restoring IL-10 levels. These six flavonoids from two subclasses revealed the following antioxidant capability: P > EC, EGC > EC, Q > T, Q > R. Our results indicate that (1) the pyrogallol, dimerization, and C2=C3 double bonds of flavonoids enhanced antioxidant activity and (2) the C3 glycosylation of flavonoids attenuated antioxidant capacity.

show abstract

Section: Introductionmentioning

confidence: 99%

“…Structural diversity has been postulated to be an important element affecting the antioxidant activities of flavonoids. Some studies have compared the antioxidant activities of flavonoid subclasses with different structures [ 13 , 14 , 15 , 16 , 17 ]: (1) The position and number of hydroxyl groups greatly affect the antioxidant activities of flavonoids. (2) The antioxidant activities of flavonoids are dependent on the degree of polymerization.…”

Section: Introductionmentioning

confidence: 99%

Comparison of In Vitro and In Vivo Antioxidant Activities of Six Flavonoids with Similar Structures

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Proanthocyanidins, a class of flavonoids, are the most studied secondary metabolites found in plants due to their antioxidant properties 10–12 . Recent studies have shown the anti-glycation potential of procyanidins, oligomeric natural compounds belonging to the class of proanthocyanidins formed from catechin and epicatechin molecules 13,14 .…”

Section: Introductionmentioning

confidence: 99%

B procyanidins of Annona crassiflora fruit peel inhibited glycation, lipid peroxidation and protein-bound carbonyls, with protective effects on glycated catalase

Justino

Franco

Silva

et al. 2019

Sci Rep

View full text Add to dashboard Cite

Advanced glycation end-products (AGEs) have been reported as results of increased oxidative stress. Consequently, the search for new antioxidant and anti-glycating agents is under intense investigation. Plant-derived procyanidins have previously demonstrated anti-glycation properties. Thus, this study aimed to isolate procyanidins from Annona crassiflora fruit peel, a species from the Brazilian Savanna, and investigate their antioxidant and anti-glycation effects. Free radical scavenging and quenching properties, formation of reactive oxygen species (ROS), AGEs, protein carbonyl and thiol groups, lipid peroxidation, crosslinked AGEs, as well as glycated catalase activity, were analyzed. In addition, in silico assessment of absorption, distribution, metabolism, excretion and toxicity was carried out. The procyanidins-enriched fraction, named here as F7, showed high antioxidant and anti-glycation capacities, with inhibitory activities against lipid peroxidation, and AGEs and ROS formation. In addition, there were reductions in AGEs-induced crosslinks and protein carbonyls and protective effects against oxidation of thiol groups and glycated-catalase. ADMET predictions of F7 showed favorable absorption and distribution, with no hepatotoxicity or mutagenicity. Together, our results support the anti-glycation activities of the procyanidins-enriched fraction from A. crassiflora, and suggest that these effects are triggered, at least in part, by scavenging free radical and dicarbonyls intermediates.

show abstract

“…Fragment 496.70 ([M − 286 + H] + ) represents the loss of the pyrogallol group and 3-DG, forming the A, B and C rings of EGCG and 3-DG. Chen et al [ 34 ] showed that in the adduct of catechin and methylglyoxal ( m / z 433), the fragment ion at m / z 361 represents the loss of methylglyoxal. A similar result was also obtained for epicatechin–methylglyoxal adducts.…”

Section: Resultsmentioning

confidence: 99%

Reduction of 3-Deoxyglucosone by Epigallocatechin Gallate Results Partially from an Addition Reaction: The Possible Mechanism of Decreased 5-Hydroxymethylfurfural in Epigallocatechin Gallate-Treated Black Garlic

Lin

Lee

et al. 2021

Molecules

View full text Add to dashboard Cite

5-Hydroxymethylfurfural (5-HMF) is a harmful substance generated during the processing of black garlic. Our previous research demonstrated that impregnation of black garlic with epigallocatechin gallate (EGCG) could reduce the formation of 5-HMF. However, there is still a lack of relevant research on the mechanism and structural identification of EGCG inhibiting the production of 5-HMF. In this study, an intermediate product of 5-HMF, 3-deoxyglucosone (3-DG), was found to be decreased in black garlic during the aging process, and impregnation with EGCG for 24 h further reduced the formation of 3-DG by approximately 60% in black garlic compared with that in the untreated control. The aging-mimicking reaction system of 3-DG + EGCG was employed to determine whether the reduction of 3-DG was the underlying mechanism of decreased 5-HMF formation in EGCG-treated black garlic. The results showed that EGCG accelerated the decrease of 3-DG and further attenuated 5-HMF formation, which may be caused by an additional reaction with 3-DG, as evidenced by LC-MS/MS analysis. In conclusion, this study provides new insights regarding the role of EGCG in blocking 5-HMF formation.

show abstract

Structure-activity relationship of procyanidins on advanced glycation end products formation and corresponding mechanisms

Cited by 57 publications

References 38 publications

Comparison of In Vitro and In Vivo Antioxidant Activities of Six Flavonoids with Similar Structures

Comparison of In Vitro and In Vivo Antioxidant Activities of Six Flavonoids with Similar Structures

B procyanidins of Annona crassiflora fruit peel inhibited glycation, lipid peroxidation and protein-bound carbonyls, with protective effects on glycated catalase

Reduction of 3-Deoxyglucosone by Epigallocatechin Gallate Results Partially from an Addition Reaction: The Possible Mechanism of Decreased 5-Hydroxymethylfurfural in Epigallocatechin Gallate-Treated Black Garlic

Contact Info

Product

Resources

About